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The entire baseball world comes together this week in San Diego for MLB’s annual winter meetings. It’s the time of year when rumors are flying, deals are made and fans can be overwhelmed with the flood of information.

This special time of the offseason is unlike any other. A moment when every general manager and agent are in the same building means trade and contract discussions will be as frequent as breathing.

The 2019 winter meetings could be the best in years with so many top names available in free agency on the trade market. Before the action begins, though, there are vital questions surrounding everything that will happen this week.

Here are the burning questions heading into MLB’s winter meetings that will headline this week’s action.

Will any of the elite free agents sign during the winter meetings?

Gerrit Cole, Anthony Rendon and Stephen Strasburg entered this offseason as the top free agents, and all three remain available. Now is the perfect time for sides to get a deal done. The question is which, if any, player(s) will sign this week?

It’s improbable that Cole signs this week with teams just now making initial offers. Fortunately, Strasburg is expected to sign fairly quickly and what better time than in the city where he grew up to make it happen. He should be the overwhelming favorite to sign during the meetings among the elite free agents, but don’t be surprised if his ex-teammate gets a deal done as well.

What teams could be the “mystery team” for top free agents?

It’s the tradition everyone enjoys more than any other. Every offseason we hear about this secretive team that is hot after top free agents, from the shadows, and could surprise everyone. So, who are the clubs that could surprise?

For one, the San Francisco Giants. The team has been linked to Gerrit Cole at times this winter and there’s reportedly mutual interest. Beyond San Francisco, the Minnesota Twins and Arizona Diamondbacks could both take aggressive approaches and one big move could change everything at the winter meetings. Finally, keep an eye on the Toronto Blue Jays, who have their core infield in place but could greatly use an impact talent in their rotation to lift them into the spotlight.

Who is the surprise player that could be traded this week?

This is arguably the best part of the winter meetings. Everyone knows who is available in free agency, but MLB always finds a way to surprise fans with a trade that very few saw coming.

The Chicago Cubs trading All-Star catcher Willson Contreras would be interesting, but teams are already expecting him to be available. Instead, All-Star first baseman Josh Bell is the player to watch. He’s only 27, coming off a season with 37 home runs and is under team control for the next three seasons. Pirates general manager Ben Cherington is open to moving anyone and Bell can land the type of prospects that could change Pittsburgh’s future.

What will the Yankees and Dodgers do?

MLB’s two most prominent teams are facing the most pressure to make big moves. The Dodgers are coming off a first-round playoff exit after winning 106 games. Meanwhile, the Yankees have now gone a decade without appearing in the World Series. Obviously, this is unacceptable to both organizations and fan bases.

Fittingly, Los Angeles and New York are pursuing the same marquee free agents. We’ll certainly see agents use each organization as leverage, making the winter meetings even more entertaining. Both teams will remain heavily involved on Cole and Strasburg, while also exploring the current asking prices on All-Star sluggers Kris Bryant and Francisco Lindor. Ultimately, we’ll probably see both teams make big moves that can help them reverse their playoff misfortune next year.

Which former MVP is likeliest to be traded?

Any time there’s even a hint that a team is willing to trade an MVP-caliber player, the ears of every general manager perk up across the league. Whether the Boston Red Sox and Chicago Cubs are actively shopping Mookie Betts and Kris Bryant or just testing the market, opposing clubs won’t stop asking about them this week.

Between the two, Bryant is more likely to be dealt. Chicago’s front office is reportedly “aggressive and determined” to move someone this offseason, according to ESPN’s Jeff Passan. It’s a different stance than in Boston, where the Red Sox want to slash payroll with their efforts focused on offloading expensive pitchers. It remains unlikely that either player is traded, but Bryant seems far more likely to pack his MVP award and move to a new city.

Will MLB conclude its Astros’ sign-stealing investigation this week?

It’s the story that captured the attention of every sports fan early in the offseason. From the moment we first learned about MLB’s investigation into Houston’s alleged sign-stealing in 2017 to the details that have come out since. Suddenly, the leaks seemed to stop a few weeks ago and everyone’s focus shifted to free agency.

The silence will end this week in San Diego. Commissioner Rob Manfred will face reporters and be asked countless questions about the league’s investigation. Meanwhile, there’s nothing people love more than talking at the winter meetings and that will also provide more information. The cloud of the scandal is already in San Diego, it will either stay there the entire week, or MLB will address it and potentially even announce discipline for the Astros.

Matt Johnson
NFL, MLB & college football writer for Sportsnaut. Graduated from San Diego State University with BA in Journalism, 2019. Grew up in Sacramento, now based in Indianapolis. Seen on MSN. Previously: eDraft, The Connection, With the First Pick